One Last Shot
by Kristi's Stories
Summary: Captain Jack Sparrow had experience with women; he knew what they were like. He knew how to please a woman or how to easily tick her off. Nevertheless, women loved Jack. But this woman, dressed as a boy and calling him Mr. Smith was a change, and an annoying one at that. How is he expected to steal a ship in Port Royal with her following him around, claiming he stole her shillings?
1. Shillings

"Would you stop paying attention to the idiot and listen to me?" Catalina snapped, feeling the heat of Port Royal get to her. The man and the young Haitian boy looked her up and down before the man walked away from her, ignoring her words completely. "What-I, Hey!"

She followed closely behind them as he made his way towards the now sunken boat by the dock and the ' _idiot'_ who most likely caused it to sink. She glanced at the man and instantly knew it was a pirate but kept her mouth shut. If she called out a pirate, he would surely call her out as well.

"Hold up there, you!" She heard the man and perked up, thinking he was finally paying attention to her. She groaned, seeing him face the pirate man.

' _What I wouldn't do to be with Roberts again on The Royal Fortune. Even if I must be dressed as a man again.'_

"…tie up the boat to the dock."

She and the pirate man glanced to the sunken boat, and she snorted – catching only the attention of the pirate. The other man and the boy continued to ignore her existence completely. _'Perhaps I should have dressed as a man today.'_

"And I shall need to know your name." The man stated, catching the attention of the pirate away from her, for which she was grateful. She never liked others staring at her for too long when she was dressed as a woman.

The pirate placed three shillings onto the logbook the man held, and her eyes widened. She hardly had anything to her name. How did he have three shillings? She looked over him and raised an eyebrow but shook her head.

It's not wise to pickpocket another pirate. It's very likely they know all the same tricks you do.

" _What…to three shillings, and…the name?"_

Catalina glanced around, feeling as though any attempt to get the man's attention would be futile. Her eyes caught a bag sitting idly by on a stand. She whimpered. There were most likely shillings in there and she had not had a bite to eat in two days, and the seawater was ghastly to the taste.

" _Welcome…Mr. Smith."_

She ignored the rest of the conversation and turned away, hearing the man steps fade the other way. She made a grab for the bag before the back of her hand was smacked, causing her to jerk her hand back.

"Who the hell do-" She paused, coming face to face with the pirate who only shook the bag in front of her, listening to the ringing of shillings inside. The noise made her stomach quench and she glared up at him. "That's mine."

"Actually, it's his, lass." With that, the pirate man strode away with her shillings.

She would **not** give up so easily.

Catalina followed closely behind as she did with the logbook man. The pirate man turned to face her, and paused in his tracks to look at her. "What do you want?" He stepped away from her as though she was a rodent of some kind.

"I want my bag of shillings, Mr. Smith."

"It's not yours, lass."

"I saw it first; I was going to take it. It's mine." She said firmly, looking into his eyes.

He stared back before abruptly turning away and continuing to walk in an odd fashion. Catalina could tell there was something up with this pirate; something not quite right, yet she continued to follow. She wanted the shillings.

Catalina paused in her tracks, seeing him make his way towards a very, _very_ fancy looking ship. _'What in the hell does this idiot think he is doing?'_

"Mr. Smith, I hope your intention isn't to simply walk up to a guarded ship and try to take it." For the first time, he ignored her words. She smirked. "I would imagine no pirate is that stupid."

"That is exactly my intention." He paused in his step and turned to face her. "You shouldn't pass that word lightly, lass; especially in a place such as Port Royal, where they will hang a pirate as lovely as _you_."

Catalina stiffened up, and pursed her lips together. "I need those shillings," she stepped close to him. "I haven't eaten in two days, Mr. Smith. Not since I've gotten here and that bloody man at the docks won't acknowledge me."

"Firstly, my name is not Mr. Smith." He placed his hand on his chest and grinned. "I am Captain Jack Sparrow, lass."

Catalina scoffed, shaking her head. "Am I supposed to be impressed, Captain Jack Sparrow?" She smirked. "I sail with a very well-known pirate, so it takes a lot for me to be impressed."

"Why aren't you on his ship then?"

Catalina swallowed. "I was separated from him and I had no choice but to come here." She raised her brown eyes to look into his. "Captain," She grasped his shoulder lightly, tilting her head to the side. "If you would be so kind, could you help me find him?" She lifted a hand to her brown wavy hair and twirled a strand for good measure.

Jack smiled, and simply shrugged her hand off. "Listen, lass. I've had my fair share of experience with women and I know when I'm being taken for a fool." He shook his head. "Look for your pirate on your own."

With that, Jack turned away from Catalina and continued on to the ship in the distance.

"Hey! I still want the shillings!" Catalina shouted, following closely behind but the pirate ignored her yells. She huffed and rolled her eyes, continuing to follow him in silence to the dock.

* * *

 **Please leave reviews if I should continue with the story or not. Reviews are greatly appreciated. Let me know what you think of the OC, and her interaction with the infamous Jack Sparrow.**

I am aware that it's not historically accurate with Bartholomew Roberts of the Royal Fortune being alive at this time period but I did change it to fit the OC's backstory. Of course, this is only a minor detail to the character and does not play such a huge role to the story itself.

Have a lovely day!


	2. Interceptor

Jack turned to glance at Catalina for a moment and stopped in his step, watching her. "What are you doing, lass?"

Catalina groaned. "Does it matter to you, Mr. Sparrow?" She asked, twisting her hair around her hand and tucking it underneath her hat. "My name is Carlos, not lass." She felt around her chest, and Jack turned around at that moment.

"I want my shillings." She commented loudly, watching the pirate start to walk away again. "I will get it one way or another, Jack!"

She continued to follow him, until they approached the docks where the big ship was. Catalina had to admit, Jack had good taste. "What are you going to do if you get caught?" She asked, tapping his shoulder.

He ignored her and continued to walk ahead of her. "You mean, if we get caught?"

Catalina raised an eyebrow at his back, and she laughed nervously, following him onto the dock now. "No, I meant what are you going to do if you-" Catalina went quiet as two men scrambled to stand in front of her and Jack. They looked fiercely at Jack and her.

"This dock is off limits to civilians."

"I'm very sorry, we didn't know." Catalina sent a pointed look to Jack. ' _What is this we crap?_ ' she thought. "If we see one, we shall inform you immediately."

Jack took a hold of Catalina's hand and quickly tried to maneuver around the two but they were quick as well and stepped in their way. Jack pursed his lips in thought. "Apparently, there is some sort of high toned and fancy to do up at the fort, eh? How could it be that two upstanding gentlemen such as yourselves did not merit an invitation?"

The thin guard seemed a bit at a loss for words before replying. "Someone has to make sure this dock says off limit to civilians." The larger one nodded in agreement and Catalina felt as though these two were left behind to do a pointless task.

"It's a fine goal to be sure but it seems to me that a…" Jack pulled Catalina along with him, apparently attempting to go around the two once again. Alas, they were thwarted as the two guards kept a firm stance in front of them. "A ship like that," he pointed to a far-away ship. "Makes this one here a bit superfluous, really."

"Oh, the Dauntless is the power in these waters, true enough, but there's no ship as can match the Interceptor for speed."

Jack put a finger to his chin, deep in thought. "I've heard of one, supposed to be very fast – nigh, un-catchable…The Black Pearl."

The larger one laughed mockingly. "Well," he made a pointed look at the both of them. "There's no _real_ ship as can match the Interceptor."

The thin one made a side-ways glance to the other guard. "The Black Pearl is a real ship."

The larger one looked in disbelief at Jack and Catalina before looking back at his companion. "No, no it's not."

"Yes, it is, I've seen it."

"You've seen it?" Catalina resisted the urge to groan. This was such a useless conversation. The Black Pearl was indeed a real ship, or at least that is what Robert had told her.

"Yes."

"You haven't seen it." He shook his head.

The thin one nodded. "Yes, I have."

Catalina glanced at Jack to see he was no longer amused by this conversation as well.

The larger one leaned into the thin one's face and spoke in a low voice. "You've seen a ship with black sails, that's crewed by the damned and captained by a man so evil that Hell itself spat him back out?"

Catalina raised an eyebrow; that was quite a dramatic description. This man's story-telling skills could send Robert on a run for his money.

"No." The thin one answered in a quiet voice.

"No." The other one echoed, a satisfied grin coming onto his face.

"But I have seen a ship with black sails."

Jack pulled on her hand, and she looked to him. He nodded his head to the ship and pulled her along with him, leaving behind the two bantering guards. Catalina resisted the urge to laugh at how easy it was to slip under the radar of those two.

"Jack," she whispered in order to not be heard. "They'll eventually stop and see us on their ship."

Jack nodded as they boarded the ship together. "I am well aware, lass. Just go with it." He smiled as he placed his hands on the wheel and looked out to the sea. Catalina recognized the look on his face. It was the look of longing to be out at sea, which almost every pirate wore once they were grounded somewhere that was not above water.

"Hey! You two!" Catalina jumped at the yells and turned to see the two soldiers running over to the ship. The thin one boarded the ship and drew their weapon, pointing it at Jack and her as they stood firmly in front of them. "Get away from there!"

"You don't have permission to be aboard there, mate!" The larger one yelled, coming up behind the other one and pointing his weapon specifically at Jack.

"I'm sorry, it's just – it's such a pretty boat." He smiled. "Ship." He quickly corrected himself and looked to Catalina with a small smile on his face.

' _Is this amusing for him? We're trapping on a ship, cornered by two idiots with weapons_.' She held her hands up in defense, not wanting to be killed today of all days. If she were going to die, it would be on Robert's ship.

"What are your names?"

Jack nodded. "Smith, or Smithy, if you like." He placed a hand on Catalina's shoulder and grinned. "This here is Carlos, my Cabin Boy."

Catalina looked so quick at Jack, a pain shot through the side of her neck. "Ah," she groaned, rubbing her neck slowly. "Yes, what he said." She muttered, feeling more trapped than ever.

"What's your purpose in Port Royal, Mr. Smith and…Cabin Boy?" The larger one asked, looking Catalina up and down in question.

"Yeah, and no lies." The other one added, continuing to point his weapon at the both of them.

"Well, then, we confess." Catalina raised an eyebrow at Jack as he walked in front of her to face the two men. "It is our intention to commandeer one of these ships, pick up a crew in Tortuga, raid, pillage, plunder and otherwise pilfer our weasely black guts out."

Catalina look to the two guards in fear, wondering what would happen now due to Jack's recklessness. ' _You're most possibly the worst pirate I've ever had the misfortune of meeting, Jack Sparrow_.' She stepped back, thinking maybe she should just jump into the waters and swim as fast as she could.

On the other hand, Jack had her shillings still.

"I said no lies!"

"I think he's telling the truth."

"If he were telling the truth," This time, Catalina vocally groaned her annoyance. "He wouldn't have told us."

"Unless, of course," Jack started, making Catalina's hands clench up in fists. He would only make things worse from here on out, she was sure of it. "He knew you wouldn't believe the truth even if he told it to you."

"Idiots." Catalina turned away, ignoring any more words that came from Jack's mouth or the other two. She covered her face and groaned lightly. How did all of it go so wrong? She was stuck in Port Royal with an idiot pirate who had just made her his unofficial Cabin Boy. "Robert, where in the hell are you?" She muttered, looking out to sea.

She jumped, hearing a splash and looked to see the waters moving by the cliff. She saw a rather large figure lingering in the water, sinking. It was too large to be a fish. "Jack?" She turned and looked at the three men who just stood there in silence, looking at the shifting water as well before they ran over to stand beside her.

It was a woman in the water, Catalina noticed but it appeared to her and the others that this woman was not making any efforts to reach the surface.

Jack pointed out to water and leaned to the larger guard. "Will you be saving her then?"

"I can't swim."

Catalina looked to him with a sharp glare as Jack looked to the other guard for help, who only shook his head in response.

"Pride of the King's Navy you are." Jack began take off his effects, handing his hat to Catalina and handing the rest of his effects to the guards. "Do not lose these." Before Catalina could voice any protest, Jack dived into the water.

Catalina stood there, clutching onto Jack's hat in fear. He had left her behind with two guards who could easily grab her at any moment and turn her in if they realized she was a pirate. She stepped back but stopped when she noticed the water suddenly quiver from where Jack was.

"What was that?" The thin one looked to the larger one and to her. She shrugged her shoulders along with the larger one, suddenly feeling the winds change.

' _Something doesn't feel right.._ ' She thought and jumped, yelping in surprise when she was suddenly grabbed by the larger guard.

"Come with us, now. We're getting off this ship, before someone sees we've let you on."

As the three of them headed off the ship, they noticed Jack climbing onto the dock, holding the woman over his shoulder. The two guards threw his effects and their weapons to the side to help him with the unconscious woman.

Catalina resisted the urge to grab one of their weapons for defense.

"She's not breathing!" Instead, Catalina rushed over to them, and watched as the guards struggled to do something to help the unconscious woman.

"Move!" Jack pushed the thin one aside and took a knife, cutting open the woman's corset, and instantly, the woman sprang back to consciousness, spitting up the water from her lungs. Catalina looked away, her cheeks red from seeing the woman without her undergarments. Catalina had seen worse but only from a pirate – not from what seemed to be a noble woman of sorts.

The larger one looked at Elizabeth in shock, and Catalina had almost snapped at him to look away – the woman wasn't decent, for goodness sake. "Never would've thought of that."

"Clearly, you've never been to Singapore." Jack commented, overlooking the woman before he took hold of something that was hanged around her neck. Catalina's eyes widened at the coin in Jack's hand. She recognized it from one of Robert's stories. "Where did you get that…?" He asked the stuttering woman quietly.

Jack looked up as a sword was drawn in front of his face and Catalina looked up to see nearly half of the King's Navy surrounding them now. She swallowed, still clutching onto Jack's hat in fear.

' _What have I gotten myself into?'_


	3. Lad

Catalina spit, trying to get the taste of hay out of her mouth – she could taste something in the air, amazing that even the _air_ tasted disgusting.

Looking up, she paused, seeing a gate in front of her. As she glanced around, she noticed she was in a cellblock with other pirates. "Jack." She muttered, feeling her face heat up in anger.

"Oi, you." She ignored the calls from the man in the cell next to her. "What's your name, boy?"

She ignored them and walked up to the door of her cell, pulling at it with all her strength. She screamed in frustration when she realized there was no way out.

Plopping down onto the ground, she crossed her legs and tried to remember her last memory. ' _How did I end up in here again?_ '

 _Catalina stood behind Jack, while the Elizabeth girl placed his effects on him, ignoring his comments about his supposed 'goods'. Catalina was looking for an escape plan, any kind of escape plan but looking behind her, all she saw was ocean._

' _Damn you, Jack.' She thought, chewing on her bottom lip._

 _Jack wrapped a chain around Elizabeth's neck, and addressed half of the King's Navy, gun pointing to the Elizabeth's head. "Gentlemen," he smiled down at Elizabeth. "M'lady, you will always remember this as the day that you almost caught Captain Jack Sparrow."_

 _Catalina scoffed. What exactly was his escape plan here?_

 _Jack looked back at her and flashed a quick smirk. "And his cabin boy!"_

 _Oh, she could have strangled him immediately with that chain. That was until Jack pushed Elizabeth towards the crowd and grabbed Catalina's hand, quickly wrapping it around his waist. "Might want to hold on tight, love."_

 _Catalina rolled her eyes, holding around his waist. Jack took out his sword and sliced at a rope, while holding the other end. To say Catalina was unprepared is a gigantic understatement._

 _Her grip was not tight enough, and as they rose above the ground, Catalina lost her grip on his waist and went crashing back down on the dock, hitting her head and falling into darkness._

'Shit.' She shook her head, and swallowed. The reality of where she was, was finally hitting her and she wanted nothing more but for Robert and his crew to barge in and save her.

However, Robert was far away now and an idiot pirate had landed her in a cell.

"Jack Sparrow is dead." She muttered to herself.

"Oi, I asked for a name!"

Catalina looked to the man in the cell next to her. He was larger in stature and short, with balding spots on his shiny, sweaty head. His beard was long and scraggly, as though rats had made their nest there.

"Carlos." She answered, swallowing. She was stuck here for the time being, it would not hurt to make new acquaintances. "Does there happen to be another pirate around? Cocky, arrogant, goes by the name 'Captain' Jack Sparrow?" She asked, hoping Jack was in the same situation he had put her in.

"Jack Sparrow, eh?" The man chuckled darkly and shook his head. "Sorry but no, I haven't seen Jack around."

"You know him?" She asked, raising an eyebrow. It seemed Jack did have a reputation after all.

"In a manner of speaking." He replied, narrowing his eyes at her. "Carlos, you said?"

She nodded and bit her lip, nervous if the man could see past her disguise. In her defense, she had no access to cloth to bind her chest so she could only be thankful that her appearance had always given off the impression of a scrawny little boy. "Yeah, Carlos del Corona."

"Fancy name." The man commented, leaning on the cell wall. "Where you from, boy?"

"What about you?" She snapped. "You're practically interrogating me – what about your story?"

The man chuckled, and turned away from her to retreat to whatever little privacy he had in his own cell.

' _Where the hell is Jack?_ ' She thought, feeling her hands curl up into fists. She could kill Jack with her bare hands with all the anger she had. _'Then again – he did tell me to hold on tight. It's not all his fault.'_

Catalina sat up straight as she heard a door slam open, and as though her prayers had been answered; guards came down a flight of stairs, carrying an unconscious Captain Jack Sparrow.

She stood up and pointed to the guards. "Oi! That is my Captain you are carrying! What did you do to him?" She asked, feigning concern for the unconscious Jack.

The guards said nothing but glanced to each other. They walked to her cell door, unlocking it quickly. After throwing in the unconscious Jack carelessly, they locked up the cell as quickly as they unlocked it.

"Hey! I asked you lot a question!" She yelled, as the guards turned away from her and went back up the stairs to what she assumed was the only exit in the place.

Catalina looked down to the unconscious Jack, and felt her cheeks heating up in anger once again. She did the only thing she could think of in that moment and slammed her foot into his side. "Wake up!" She hissed.

There was no response from the unconscious pirate. She kicked him once more.

"You know, love…that is not a proper way to wake up a man." She heard him mutter.

"Yes, I suppose the way most women wake you up is by-" She paused, realizing her anger was getting the best of her. She shook her head. "Are you alright, Jack?"

"Never better." Jack answered, sitting up and narrowing his eyes at her while holding his side. "You got quite the strength for a bony lass."

"Quiet." She snapped, looking back to the large man in the cell next to her. He was not paying attention. "I'm still Carlos to you, Jack – keep it that way. Call me lad, not lass."

"You know, a woman pirate once pretended to be pregnant – got herself nine months of relaxing in a cell."

Catalina sighed. "Jack, for one thing, she died in the cell when she got sick – don't believe all stories and second of all, they can have someone check me." She muttered the last part, her cheeks heating up.

Jack raised an eyebrow and the corner of his lip pulled up into a small smirk. "Your face tells me you've never lain with a man."

Catalina's eyes widened, surprised that Jack had stated the truth so bluntly. Although it was true, Catalina preferred to keep it quiet – not a topic up for discussion. "Jack, you need to find a way to get me out of here. I'm not going to the gallows any time soon – I need to find Robert."

Jack narrowed his eyes. "What is with you and this supposedly famous Captain Robert?" He asked.

Catalina sighed. "Robert is a good man, Jack. He took me in when he could have killed me. I owe my life to him."

Jack laid down, putting his arms behind his head. He nodded to Catalina. "Is he aware of your situation in your trousers?"

' _What a disgusting way to ask._ ' Catalina clicked her tongue and shook her head. "No, he doesn't." She said quietly, feeling ashamed. She owed Robert so much but never told him the truth that she was a woman.

"You're afraid he'll throw you overboard?" Jack asked.

Catalina laughed bitterly, crossing her arms. "He created a code on his ship, Jack. He does, in fact, throw women overboard."

"Unusual situation you've found yourself in." Jack muttered.

"Get me out of here."

Jack sighed, closing his eyes and pinching the bridge of his nose. "I'll think of a plan, lass." He pat the floor next to him. "For now, come and curl up to your captain."

The smirk on his face told Catalina she would regret letting him know that she was a virgin. "No, thank you, and it's _lad_." She turned away and sat on the opposite side of the cell.

The two sat in silence until they heard it, the beautiful ringing – the beautiful ringing of…keys! They both sat up and watched as a filthy furred dog walked past their cell. Instantly, they stood up and pressed up against the cell wall to watch it walk away.

"You're better get those keys." Catalina muttered.

"Just be patient, lass."

"Lad! For the last time, I am a boy!"

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